1043577-37-2

Basic information

• Product Name: (5R,8S,11S)-8-isopropyl-5-methyl-11-((E)-4-(tritylthio)but-1-en-1-yl)-10-oxa-3,17-dithia-7,14,19,20-tetraazatricyclo[14.2.1.12,5]icosa-1⁽¹⁸⁾,2⁽²⁰⁾,16⁽¹⁹⁾-triene-6,9,13-trione
• Synonyms: (5R,8S,11S)-8-isopropyl-5-methyl-11-((E)-4-(tritylthio)but-1-en-1-yl)-10-oxa-3,17-dithia-7,14,19,20-tetraazatricyclo[14.2.1.12,5]icosa-1⁽¹⁸⁾,2⁽²⁰⁾,16⁽¹⁹⁾-triene-6,9,13-trione
• CAS NO: 1043577-37-2
• Molecular Weight: 738.996
• Mol File: 1043577-37-2.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (5R,8S,11S)-8-isopropyl-5-methyl-11-((E)-4-(tritylthio)but-1-en-1-yl)-10-oxa-3,17-dithia-7,14,19,20-tetraazatricyclo[14.2.1.12,5]icosa-1⁽¹⁸⁾,2⁽²⁰⁾,16⁽¹⁹⁾-triene-6,9,13-trione(CAS DataBase Reference)
• NIST Chemistry Reference: (5R,8S,11S)-8-isopropyl-5-methyl-11-((E)-4-(tritylthio)but-1-en-1-yl)-10-oxa-3,17-dithia-7,14,19,20-tetraazatricyclo[14.2.1.12,5]icosa-1⁽¹⁸⁾,2⁽²⁰⁾,16⁽¹⁹⁾-triene-6,9,13-trione(1043577-37-2)
• EPA Substance Registry System: (5R,8S,11S)-8-isopropyl-5-methyl-11-((E)-4-(tritylthio)but-1-en-1-yl)-10-oxa-3,17-dithia-7,14,19,20-tetraazatricyclo[14.2.1.12,5]icosa-1⁽¹⁸⁾,2⁽²⁰⁾,16⁽¹⁹⁾-triene-6,9,13-trione(1043577-37-2)

Safety Data

• Hazardous Substances Data: 1043577-37-2(Hazardous Substances Data)

Upstream product

• 1043577-34-9 (S,E)-2-(trimethylsilyl)ethyl 3-(((S)-2-((R)-2'-(((tert-butoxycarbonyl)amino)methyl)-4-methyl-4,5-dihydro[2,4'-bithiazole]-4-carboxamido)-3-methylbutanoyl)oxy)-7-(tritylthio)hept-4-enoate 
• 1191242-43-9 C₄₀H₄₄N₄O₅S₃ 
• 297165-32-3 methyl 2-(tert-butoxycarbonylaminomethyl)thiazole-4-carboxylate 
• 1033814-13-9 (R)-2-(2-((tert-butoxycarbonylamino)methyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylic acid 
• 1137735-74-0 (S,E)-2-(trimethylsilyl)ethyl 3-(((S)-2-amino-3-methylbutanoyl)oxy)-7-(tritylthio)hept-4-enoate 
• 71904-80-8 2-((tert-butoxycarbonylamino)methyl)thiazole-4-carboxylic acid 
• 182120-82-7 2-(tert-butoxycarbonylaminomethyl)-1,3-thiazole-4-carboxamide 
• 251294-64-1 2-[N-(tert-butoxycarbonyl)aminomethyl]thiazole-4-carbonitrile 
• 1092363-38-6 C₅₅H₅₄N₄O₇S₃ 
• 1092363-37-5 (R)-methyl 2-(2-(((3S,4E)-3-hydroxy-7-(tritylthio)hept-4-enamido)methyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylate 
• 1092363-40-0 (4R)-methyl 2-(2-((8S)-1-(9H-fluoren-9-yl)-5-isopropyl-3,6,10-trioxo-8-((E)-4-(tritylthio)-but-1-enyl)-2,7-dioxa-4,11-diazadodecan-12-yl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylate 
• 3695-77-0 triphenylmethanethiol 
• 150350-28-0 S-trityl 3-mercaptopropionaldehyde 
• 180973-22-2 (2E)-5-[(triphenylmethyl)thio]-2-pentenal 

Downstream Products

• 1009815-87-5 largazole 
• 1338230-01-5 C₂₈H₃₄N₄O₅S₃ 

Relevant articles and documents

METHOD FOR PREPARING LARGAZOLE ANALOGS AND USES THEREOF

Analogs of largazole are described herein. Methods of treating cancer and blood disorders using largazole and largazole analogs and pharmaceutical compositions comprising the same are additionally described herein. Methods for preparing largazole analogs are likewise described.

Largazole and analogues with modified metal-binding motifs targeting histone deacetylases: Synthesis and biological evaluation

The histone deacetylase inhibitor largazole 1 was synthesized by a convergent approach that involved several efficient and high yielding single pot multistep protocols. Initial attempts using tert-butyl as thiol protecting group proved problematic, and synthesis was accomplished by switching to the trityl protecting group. This synthetic protocol provides a convenient approach to many new largazole analogues. Three side chain analogues with multiple heteroatoms for chelation with Zn2+ were synthesized, and their biological activities were evaluated. They were less potent than largazole 1 in growth inhibition of HCT116 colon carcinoma cell line and in inducing increases in global H3 acetylation. Largazole 1 and the three side chain analogues had no effect on HDAC6, as indicated by the lack of increased acetylation of α-tubulin.

Concise total synthesis of largazole

The concise total synthesis of largazole was accomplished. The key step included the use of the Nagao thiazolidinethione auxiliary for the diastereoselective acetate aldol reaction and it acts as an acylating agent for the peptide formation.